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PubMed1993

Selective inactivation of glyceraldehyde-3-phosphate dehydrogenase by vinyl sulfones.

Incubation of glyceraldehyde-3-phosphate dehydrogenase with vinyl sulfones resulted in a pseudo first-order loss of enzyme activity. The selective inactivation of the enzyme by vinyl sulfones is suggested from the structural requirement analysis and the enzyme susceptibility test. The enzyme inactivation was strongly reduced in the presence of NAD or glyceraldehyde-3-phosphate, and the prior treatment of the enzyme with 5,5'-dithio-bis-(2-nitrobenzoic acid) prevented the enzyme from the inactivation by vinyl sulfones (> or = 90%). Moreover, the early rapid phase of inactivation was much more responsive to L-cysteine reactivation, compared with the slower phase. Based on these results, it is proposed that vinyl sulfones inactivate the enzyme by inducing the oxidation of cysteine residue and/or covalent binding to cysteine residue in active site.

Animals↗
PubMed1992

Synthesis of sulfonate analogs of bile acids.

Sulfonate analogs of C23 and C24 bile acids were synthesized from norcholic, norchenodeoxycholic, norursodeoxycholic, nordeoxycholic, norhyodeoxycholic, cholic, deoxycholic, hyodeoxycholic, and lithocholic acids. The principal reactions used were (1) reduction of the bile acids with NaBH4 to the corresponding bile alcohols, (2) selective tosylation of the terminal hydroxyl group, (3) iodination of the tosyl esters with NaI, and (4) treatment of the iodides with Na2SO3 to form the sulfonate analogs of the bile acids. The sulfonate analogs showed polarity similar to that of taurine-conjugated bile acids on thin-layer chromatography. The carbon 13 nuclear magnetic resonance spectral data for the sulfonate analogs were tabulated.

Bile Acids and Salts↗
PubMed2006

Use of solid-phase extraction, reverse osmosis and vacuum distillation for recovery of aromatic sulfonic acids from aquatic environment followed by their determination using liquid chromatography-electrospray ionization tandem mass spectrometry.

Three different sample preparation techniques (i) solid-phase extraction, (ii) reverse osmosis and (iii) vacuum distillation have been investigated and the recoveries were compared for determination of highly water-soluble benzene and stilbene sulfonic acids in aqueous environment by liquid chromatography with photodiode array (PDA) and electrospray ionization tandem mass spectrometry (LC-ESI-MS/MS). The recoveries were quite high using vacuum distillation (>90%) compared to solid phase extraction and reverse osmosis. The negative ion ESI mass spectra containing the peaks of quasimolecular ion [M-H]- allow the molecular mass determination of unknown compounds whereas the structures were proposed using fragments obtained from MS/MS analysis of [M-H]- ions. At lower fragmentation voltages only the quasimolecular ion [M-H]- was observed and as fragmentation voltages increased, it led to the formation of fragment ions corresponding to [M-H-SO3]-, [M-H-SO2]-, and SO3-. The detection limits were 1-28 microg/L with LC-ESI-MS. The sample collected from wastewater treatment plant was found to contain 21.1, 13.3, 12.1, 41.8 and 9.9 microg/L of cis-4,4(l)-diaminostilbene-2,2(l)-disulfonic acid (cis-DASDA), trans-4,4(l)-diaminostilbene-2,2(l)-disulfonic acid (trans-DASDA), 3-amino acetanilide-4-sulfonic acid (3-AASA), 4-chloroaniline-2-sulfonic acid (4-CASA), 2-chloroaniline-5-sulfonic acid (2-CASA), respectively.

Chromatography, High Pressure Liquid↗
PubMed2006

Biological evaluation of sulfone derivatives as anti-inflammatory and tumor cells growth inhibitory agents.

A variety of sulfone derivatives including three dimethyl arylsulfonyl malonates (1-3), two bis-(arylethenesulfonyl)-vinyl benzenes (4 and 5) and a sulfone triazole (6) were evaluated for their anti-inflammatory as well as tumor cells growth inhibitory activities in vitro. The sulfone derivatives 1, 2, 3 and 6 significantly and dose-dependently inhibited the production of inflammatory mediators such as nitric oxide (NO), and cytokines (tumor necrosis factor (TNF)-alpha and interleukin (IL)-12), in lipopolysaccharide (LPS) and interferon (IFN)-gamma activated murine peritoneal macrophages, without displaying cytotoxicity. The inhibitory mechanism is found through reducing iNOS protein expression. In addition, the derivatives 1-3 significantly arrest mitogen-stimulated spleen cells in G0/G1 stage, whereas compounds 4-6 blocked the same in the G2/M phase. Furthermore, the sulfone derivatives 3 and 6 showed dramatically reduction in the ratio of IFN-gamma to IL-4 production from mitogen-stimulated spleen cells. On the other hand, the novel compounds exhibited interesting cytotoxic activities against a panel of cell lines, particularly, 20 muM of compound 3 showed 50% cytotoxic effect on human hepatoma cell line, but has no effect on normal human peripheral blood mononuclear cells. In conclusion, compound 3 showed interesting anti-inflammatory and tumor cells growth inhibitory functions.

Animals↗
PubMed2000

Solid-phase extraction of polar hydrophilic aromatic sulfonates followed by capillary zone electrophoresis-UV absorbance detection and ion-pair liquid chromatography-diode array UV detection and electrospray mass spectrometry.

A comprehensive comparison of four different polymeric solid-phase extraction (SPE) materials for the extraction of 22 different aromatic sulfonates of environmental concern was performed. The investigated adsorbents were the polystyrene-divinylbenzene materials LiChrolut EN from Merck, Isolute ENV+ from International Sorbent Technology, HR-P from Macherey-Nagel and the new Oasis HLB poly(divinylbenzene-co-N-vinylpyrrolidone) copolymer from Waters. Different SPE parameters like the elution solvent and the drying step of the cartridges were optimized. Analyses were performed by capillary zone electrophoresis-UV absorbance detection (CZE-UV) and ion-pair liquid chromatography-diode array UV detection coupled in series with electrospray mass spectrometry (IP-LC-DAD-ESI-MS) in the negative ionization mode. LC-MS offers a higher separation efficiency than CZE. The best adsorbents were LiChrolut EN and HR-P followed by Isolute ENV+ and Oasis HLB. The recoveries for most of the onefold negatively charged aromatic sulfonates were >50% for the extraction from spiked ground water at 50 microg/l. Recoveries for LiChrolut EN and HR-P were approximately 20% higher than for Isolute ENV+. Very hydrophilic sulfonates containing more than one negative sulfonate group could not be extracted by any of the tested adsorbents.

Calibration↗
PubMed2002

Sulfoacylated poly(styrene-divinylbenzene) copolymers as resins for cation chromatography. Comparison with sulfonated, dynamically coated and silica gel cation exchangers.

Most important properties of an ion chromatographic resin are influenced by the resin matrix, the type of functional group and the ion-exchange capacity. Highly crosslinked PS-DVB resins of 5 microm diameter have been functionalized by sulfoacylation, by sulfonation and by dynamic coating over a wide range of exchange capacities. These materials allow a study of the influence of different ion-exchange sites and capacities. The influence of the degree of functionalization on resin performance is completely reverse for sulfoacylated and sulfonated resins. The HETP values for all observed analytes (Cu, Pb, Zn, Ni, Co, Cd, Mn, Ca, Mg) in a tartaric acid elution system decrease for sulfoacylated resins with increasing capacity, for sulfonated resins with decreasing capacity. The performance of sulfoacylated exchangers is better than for dynamically coated ones and far better than for sulfonated resins. The performance of silica gel based cation-exchangers such as BioSil CAT is in most cases better than observed for sulfoacylated resins.

Cation Exchange Resins↗
PubMed1998

Analysis of aromatic sulfonates in water by solid-phase extraction and capillary electrophoresis.

The separation of 14 different aromatic sulfonates of environmental concern by capillary (zone) electrophoresis (CZE) is presented. A new off-line solid-phase extraction (SPE) enrichment procedure, that is compatible with CE analysis, was developed, using the styrene-divinylbenzene adsorbent LiChrolut EN. The combined method of SPE and CE allows the determination of aromatic sulfonates in water samples in the low microgram/l range. Separations are performed with a simple sodium borate buffer at pH 9.3. Analytes are detected by UV absorbance and fluorescence emission with a Xe-lamp excitation source, and both principles are compared. The recoveries for most of the sulfonates are > 70% for the extraction from spiked tap and river water. The average method precision is < 20% for replicate analyses. Very hydrophilic sulfonates cannot be extracted by this method. The detection limit of the combined method of SPE enrichment and CE analysis is approximately 0.1 microgram/l for 200-ml water samples. The performance of the method was checked with the analysis of river and contaminated seepage water.

Calibration↗
PubMed2000

Riding the sulfur cycle--metabolism of sulfonates and sulfate esters in gram-negative bacteria.

Sulfonates and sulfate esters are widespread in nature, and make up over 95% of the sulfur content of most aerobic soils. Many microorganisms can use sulfonates and sulfate esters as a source of sulfur for growth, even when they are unable to metabolize the carbon skeleton of the compounds. In these organisms, expression of sulfatases and sulfonatases is repressed in the presence of sulfate, in a process mediated by the LysR-type regulator protein CysB, and the corresponding genes therefore constitute an extension of the cys regulon. Additional regulator proteins required for sulfonate desulfonation have been identified in Escherichia coli (the Cbl protein) and Pseudomonas putida (the AsfR protein). Desulfonation of aromatic and aliphatic sulfonates as sulfur sources by aerobic bacteria is oxygen-dependent, carried out by the alpha-ketoglutarate-dependent taurine dioxygenase, or by one of several FMNH(2)-dependent monooxygenases. Desulfurization of condensed thiophenes is also FMNH(2)-dependent, both in the rhodococci and in two Gram-negative species. Bacterial utilization of aromatic sulfate esters is catalyzed by arylsulfatases, most of which are related to human lysosomal sulfatases and contain an active-site formylglycine group that is generated post-translationally. Sulfate-regulated alkylsulfatases, by contrast, are less well characterized. Our increasing knowledge of the sulfur-regulated metabolism of organosulfur compounds suggests applications in practical fields such as biodesulfurization, bioremediation, and optimization of crop sulfur nutrition.

Amino Acid Sequence↗
PubMed1999

6-(1-Hydroxyalkyl))penam sulfone derivatives as inhibitors of class A and class C beta-lactamases II.

Two stereoselective processes for the synthesis of novel 3,6-disubstituted penam sulfone derivatives were developed. One 6beta-(1-hydroxyethyl) and four 6beta-hydroxymethyl penam sulfone derivatives were synthesized. All four 6beta-(hydroxymethyl)penam sulfone derivatives demonstrated good IC50 against both TEM-1 and AmpC beta-lactamases. Of these, 6beta-hydroxymethyl penam sulfone derivative 25 was the most active inhibitor which was able to restore the activity of piperacillin in vitro and in vivo against both TEM-1 and AmpC beta-lactamases producing organisms.

Enzyme Inhibitors↗
PubMed2001

Synthesis and human leukocyte elastase inhibitory evaluation of phosphate triesters and acyl phosphates of penam sulfides and sulfones.

The synthesis of 6,6-dibromo-3alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3a), 6alpha-chloro-3alpha-(diphenylphosphate)oxymethyl-2,2-dimethyl penam sulfone (3b), benzyl 6alpha-(diphenyl-phosphate)oxypenicillanate sulfone (4) and 6,6-dibromo-3alpha-(methylphosphate)carbonyl-2,2-dimethylpenam sulfone (12) are reported. When tested as inhibitors of human leukocyte elastase, the compound 4 proved to be the most active.

Esters↗
PubMed2001

Synthesis, DNA cleavage, and cytotoxicity of a series of bis(propargylic) sulfone crown ethers.

Compounds that couple molecular recognition of specific alkali metal ions with DNA damage may display selective cleavage of DNA under conditions of elevated alkali metal ion levels reported to exist in certain cancer cells. We have prepared a homologous series of compounds in which a DNA reactive moiety, a bis(propargylic) sulfone, is incorporated into an alkali metal ion binding crown ether ring. Using the alkali metal ion pricrate extraction assay, the ability of these crown ethers to bind Li(+), Na(+), and K(+) ions was determined. For the series of crown ethers, the association constants for Li(+) ions are generally low (< 2 x 10(4)M(-1)). Only two of the bis(propargylic) sulfone crown ethers associate with Na(+) or K(+) ions (K(a) 4-8 x 10(4)M(-1)), with little discrimination between Na(+) or K(+) ions. The ability of these compounds to cleave supercoiled DNA at pH 7.4 in the presence of Li(+), Na(+), and K(+) ions was determined. The two crown ethers that bind Na(+) and K(+) display a modest increase in DNA cleavage efficiency in the presence of Na(+) or K(+) ions as compared to Li(+) ions. These two bis(propargylic) sulfone crown ethers are also more cytotoxic against a panel of human cancer cell lines when compared to a non-crown ether macrocyclic bis(propargylic) sulfone.

Alkynes↗
PubMed2003

Vibrational frequencies and structural determinations of di-vinyl sulfone.

We present a detailed analysis of the structure and infrared spectra of di-vinyl sulfone. The vibrational frequencies of the di-vinyl sulfone molecule were analyzed using standard quantum chemical techniques. Frequencies were calculated at the MP2 and DFT levels of theory using the standard 6-311G* basis set. The structural transformation of the chemical agent bis(2-chloroehtyl) sulfide (HD, mustard gas) and the related symmetry to a previously study compounds [Spectrochim. Acta Part A 55 (1999) 121; Spectrochim. Acta Part A 57 (2001) 2417] makes the symmetry of the di-vinyl sulfone molecule an interesting candidate for study. The molecule exists normally in a C(2) configuration. High-energy forms of di-vinyl sulfone with C(S) and C(1) symmetries also exist.

Carbon↗
PubMed2005

Sorption enhancement of aromatic sulfonates onto an aminated hyper-cross-linked polymer.

A macroreticular resin adsorbent CHA-101 was aminated by dimethylamine, and a novel sorbent named M-101 was obtained. Several industrially important aromatic sulfonates including sodium benzenesulfonate (BS), sodium p-toluenesulfonate (TS), and sodium 2-naphthalenesulfonate (NS) were selected as general solutes to evaluate the performance of the newly synthesized resin particles. X-ray photoelectron spectroscope (XPS) analyses was used to determine the protonation degree of amino group at different solution pH, and the effect of pH on the sorption of these solutes onto M-101 can be explained by the ion exchange mechanism. The experimentally observed sequence of the sorption capacity of the tested organic sulfonates onto M-101 indicates that the pi-pi interaction between the solute molecule and the polymer matrix plays an important role in uptake of organic sulfonates from aqueous solution. Sodium sulfate was selected as a typical competitive inorganic anion, and improved selectivity of BS sorption over sulfate on M-101 was observed by comparison with a common macroporous weak base anion exchanger D-301. In addition, both sorption and desorption kinetics of M-101 were also found to be faster than that of D-301. Analyses of sorption isotherms and thermodynamics proved that BS sorption on M-101 was an exothermic and more selective process than on D-301. Both column tests and field applications proved M-101 to be an effective sorbent that can be used to remove aromatic sulfonates from aqueous solution.

Adsorption↗
PubMed2001

S-sulfonate determination and formation in meat products.

A treatment with cyanide for the analysis of S-sulfonates in meat and meat derivatives, after a study of the effectiveness of this agent and that of dithiothreitol (DTT), is proposed. Once the protein-bound sulfite has been released, it is determined by HPLC ion exclusion with electrochemical detection. In the assay on the reproducibility of the method, standard deviations were 7.4, 9.2, and 11.4 for mean S-sulfonate values of 69, 107, and 130 microg of SO(2)/g, respectively. Mean recovery was 91.2% for different amounts (56, 111, and 223 microg of SO(2)/g) of S-sulfocysteine added. A study was made of the formation of S-sulfonates in model systems and in meat from different species-chicken and beef-with different fat contents. In the assays with meat, two different levels of sulfite addition were used: 600 and 1200 microg of SO(2)/g. From the assays carried out in model systems with sulfite and cystine it may be concluded that one factor limiting the interaction is the accessibility to disulfide groups. The proportion of S-sulfonates in sulfited meat remains relatively constant and does not seem to be governed by the meat component, the level of sulfite addition, or the fat content. However, the latter two factors are inversely correlated with the retention of sulfite in the foods analyzed.

Chromatography, High Pressure Liquid↗
PubMed2000

Conceptually new 20-epi-22-oxa sulfone analogues of the hormone 1alpha,25-dihydroxyvitamin D(3): synthesis and biological evaluation.

New C,D-ring side-chain-modified sulfone 4a, with natural 1alpha, 3beta-hydroxyl groups but lacking the 25-hydroxyl group characteristic of the natural hormone 1alpha,25-dihydroxyvitamin D(3) (1), has been prepared and characterized. Novel synthetic features include: (1) chemoselective oxidation of only a primary silyl ether in a primary-secondary bis-silyl ether intermediate and (2) smooth reductive etherification without interference by a neighboring sulfonyl group. Sulfone 4a, but not its 1beta, 3alpha-diastereomer 4b, is powerfully antiproliferative and transcriptionally active in vitro but desirably noncalcemic in vivo. Although sulfone 4a, designed to resemble Leo Pharmaceutical Co.'s KH-1060 (3), is recognized by catabolic enzymes, the selective biological profile of sulfone 4a is likely not due to its metabolites that are formed in only minor amounts.

Animals↗
PubMed1987

Quantitative structure-activity analysis in dihydropteroate synthase inhibition by sulfones. Comparison with sulfanilamides.

A set of 25 4'-, eight 2',4'-, and five 2',4',6'-substituted 4-aminodiphenyl sulfones were tested for their inhibitory activity on dihydropteroate synthase of Escherichia coli. Linear regression analysis shows that enzymic inhibition indices correlate well with both quantum chemical and spectroscopic descriptors of the electronic structure of the common moiety 4-NH2-C6H4-SO2 of the sulfones (the above descriptors being expressed in relation to the electronic structure of the enzyme substrate, p-aminobenzoate). Therefore, the biological activity of the sulfones can be related to the electronic structural resemblance between these inhibitors and the substrate of the target enzyme. Since a similar result was previously obtained for a wide series of sulfanilamides in their different (amidic, imidic, and anionic) forms, it appears possible to consider the antibacterial sulfones and sulfanilamides as a congeneric chemical series. On the basis of the present results, the classical theory of antimetabolites would appear to take on a quantitative and sound rationale.

Dihydropteroate Synthase↗
PubMed2004

Preparation, properties, reactions, and adenosine receptor affinities of sulfophenylxanthine nitrophenyl esters: toward the development of sulfonic acid prodrugs with peroral bioavailability.

Many currently known antagonists for P2 purinergic receptors are anionic molecules bearing one or several phenylsulfonate groups. Among the P1 (adenosine) receptor antagonists, the xanthine phenylsulfonates are a potent class of compounds. Due to their high acidity, phenylsulfonates are negatively charged at physiologic pH values and do not easily penetrate cell membranes. The present study was aimed at developing lipophilic, perorally bioavailable prodrugs of sulfonates by converting them into chemically stable nitrophenyl esters. Initial stability tests at different pH values using nitrophenyl tosylates as model compounds showed that m-nitrophenyl esters were stable over a wide pH range, while the ortho and para isomers were less stable under strongly acidic or basic conditions. A series of m- and p-nitrophenyl esters of p-sulfophenylxanthine derivatives were synthesized as model compounds. The target xanthine derivatives were obtained in high yields by condensation of the appropriate 5,6-diaminouracils with 4-(nitrophenoxysulfonyl)benzoic acids in the presence of a carbodiimide, followed by ring closure with polyphosphoric acid trimethylsilyl ester. The chemical and enzymatic stability of the m-nitrophenyl esters was investigated in vitro by means of capillary electrophoresis. High stability in aqueous solution, in artificial gastric acid, and in serum was observed. However, compound 5d, used as a prototypic xanthine m-nitrophenylsulfonate, was hydrolyzed by rat liver homogenate indicating an enzymatic pathway of hydrolysis. Thus, nitrophenyl esters of sulfonic acids have a potential as peroral prodrugs of drugs bearing a sulfonate group. The nitrophenyl esters of sulfophenylxanthines were additionally investigated for their adenosine receptor affinities. They showed high affinity at A(1), A(2A), and A(2B), but not at A(3) ARs. One of the most potent compounds was 1-propyl-8-[4-[[p-nitrophenoxy]sulfonyl]phenyl]xanthine (9d), a mixed A(1)/A(2B) antagonist (K(i)A(1) 3.6 nM, K(i)A(2B) 5.4 nM) selective versus the other subtypes. As a further result of this study, the m-nitrophenoxy group was found to be a suitable protecting group for sulfonates in organic synthesis due to its high lipophilicity and stability; it can be split off under strongly basic conditions. This new protection strategy allowed for the upscaling of the synthesis of 1-propyl-8-p-sulfophenylxanthine (PSB-1115), a selective A(2B) antagonist.

Adenosine A1 Receptor Antagonists↗
PubMed1997

Structure-based design of substituted diphenyl sulfones and sulfoxides as lipophilic inhibitors of thymidylate synthase.

Six new diphenyl sulfoxide and five new diphenyl sulfones were designed, synthesized, and tested for their inhibition of human and Escherichia coli thymidylate synthase (TS) and of the growth of cells in tissue culture. The best sulfoxide inhibitor of human TS was 3-chloro-N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-4- (phenylsulfinyl)-N-(prop-2-ynyl)-aniline (7c) that had a Ki of 27 nM. No sulfone improved on TS inhibition by the previously reported 4-(N-((3,4-dihydro-2-methyl-6-quinazolinyl)methyl)-N-prop-2- ynylamino)phenyl phenyl sulfone (Ki = 12 nM). Nevertheless, one sulfone, 4-((2-chlorophenyl)sulfonyl)-N-((3,4-dihydro-2-methyl-4-oxo-6- quinazolinyl)methyl)-N-(prop-2-ynyl)aniline, was selected, on the basis of its inhibition of both TS and cell growth, for antitumor testing; it gave a 61% increase in life span to mice bearing the thymidino kinase-deficient L5178Y (TK-) lymphoma. A crystal structure of N-((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)-4-((2- methylphenyl)sulfinyl)-N-(prop-2-ynyl)aniline complexed with E. coli TS was solved and revealed selective binding of one sulfoxide enantiomer. AMBER calculations showed that the enantioselection was due to asymmetric electrostatic effects at the mouth of the active site. In contrast, a similar crystal structure of the sulfoxide 7c, along with AMBER calculations, indicated that both enantiomers bound, but with different affinities. The side chain of Phe176 shifted in order to structurally accommodate the chlorine of the more weakly bound enantiomer.

Animals↗